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P4405 Sigma

Podophyllotoxin

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Description

Biochem/physiol Actions

Inhibits microtubule assembly; antineoplastic.

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100 mg in glass bottle

50 mg in poly bottle

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Safety Information

Symbol 
GHS06  GHS06
Signal word 
Danger
Hazard statements 
Hazard Codes (Europe) 
T
Risk Statements (Europe) 
Safety Statements (Europe) 
36/37/39-45
RIDADR 
UN 3462 6.1 / PGII
WGK Germany 
3
RTECS 
LV2500000

Documents

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Protocols & Articles

Peer-Reviewed Papers

References

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Podophyllotoxins: current status and recent developments. Damayanthi, Y. and Lown, J.W. Curr. Med. Chem. 5, 205, (1998)

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Podophyllotoxin and nocodazole counter the effect of IKP104 on tubulin decay. Prasad, V., et al. J. Protein Chem. 17, 663, (1998)

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Chemical genetics reveals a complex functional ground state of neural stem cells Diamandis, P., et. al. Nat. Chem. Biol. 3(5), 268-273, (2007)

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Synthesis and antiprotozoal activity of cationic 1,4-diphenyl-1H-1,2,3-triazoles. Stanislav A Bakunov et al J. Med. Chem. 53, 254-72, (2010)

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Antimalarial ?-carbolines from the New Zealand ascidian Pseudodistoma opacum. Susanna T S Chan et al J. Nat. Prod. 74, 1972-9, (2011)

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Didemnidines A and B, indole spermidine alkaloids from the New Zealand ascidian Didemnum sp. Rhys Finlayson et al J. Nat. Prod. 74, 888-92, (2011)

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Antiprotozoal steroidal saponins from the marine sponge Pandaros acanthifolium. Erik L Regalado et al J. Nat. Prod. 73, 1404-10, (2010)

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Trypanothione reductase high-throughput screening campaign identifies novel classes of inhibitors with antiparasitic activity. Georgina A Holloway et al Antimicrob. Agents Chemother. 53, 2824-33, (2009)

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Antitrypanosomal activity of 1,2-dihydroquinolin-6-ols and their ester derivatives. Jean Fotie et al J. Med. Chem. 53, 966-82, (2010)

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Structure-activity study of pentamidine analogues as antiprotozoal agents. Svetlana M Bakunova et al J. Med. Chem. 52, 2016-35, (2009)

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Synthesis and in vitro antiprotozoal activities of dicationic 3,5-diphenylisoxazoles. Donald A Patrick et al J. Med. Chem. 50, 2468-85, (2007)

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Isoneocryptolepine, a synthetic indoloquinoline alkaloid, as an antiplasmodial lead compound. Sabine Van Miert et al J. Nat. Prod. 68, 674-7, (2005)

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Acyclic nucleoside analogues as inhibitors of Plasmodium falciparum dUTPase. Corinne Nguyen et al J. Med. Chem. 49, 4183-95, (2006)

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Synthesis and in vitro antiprotozoal activity of bisbenzofuran cations. Svetlana M Bakunova et al J. Med. Chem. 50, 5807-23, (2007)

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Limonoid orthoacetates and antiprotozoal compounds from the roots of Pseudocedrela kotschyi. Anne-Emmanuelle Hay et al J. Nat. Prod. 70, 9-13, (2007)

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Synthesis and antiprotozoal activity of cationic 2-phenylbenzofurans. Stanislav A Bakunov et al J. Med. Chem. 51, 6927-44, (2008)

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Marine natural products from the Turkish sponge Agelas oroides that inhibit the enoyl reductases from Plasmodium falciparum, Mycobacterium tuberculosis and Escherichia coli. Deniz Tasdemir et al Bioorg. Med. Chem. 15, 6834-45, (2007)

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Synthesis and evaluation of antiparasitic activities of new 4-[5-(4-phenoxyphenyl)-2H-pyrazol-3-yl]morpholine derivatives. Sabine Kuettel et al J. Med. Chem. 50, 5833-9, (2007)

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Antiprotozoal activities of heterocyclic-substituted xanthones from the marine-derived fungus Chaetomium sp. Alexander Pontius et al J. Nat. Prod. 71, 1579-84, (2008)

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Antimalarial Pyrido[1,2-a]benzimidazoles A. J. Ndakala, et al., J. Med. Chem. 54, 4581-4589, (2011)

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Quinuclidine derivatives as potential antiparasitics. Simon B Cammerer et al Antimicrob. Agents Chemother. 51, 4049-61, (2007)

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Synthesis and anti-protozoal activity of novel dihydropyrrolo[3,4-d][1,2,3]triazoles. Ya?ar Dürüst et al Eur. J. Med. Chem. 48, 296-304, (2012)

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End-binding proteins sensitize microtubules to the action of microtubule-targeting agents. Mohan R, Katrukha EA, Doodhi H, et al. Proc. Natl. Acad. Sci. U. S. A. 110(22), 8900-5, (2013)

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Structure-activity relationship of antiparasitic and cytotoxic indoloquinoline alkaloids, and their tricyclic and bicyclic analogues. Van Baelen, G., et al. Bioorg. Med. Chem. 17, 7209-7217, (2009)

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Compounds structurally related to ellagic acid show improved antiplasmodial activity. Nicole Sturm et al Antimicrob. Agents Chemother. 53, 622-30, (2009)

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Synthesis and antimalarial and antituberculosis activities of a series of natural and unnatural 4-methoxy-6-styryl-pyran-2-ones, dihydro analogues and photo-dimers. Stephen T McCracken et al Bioorg. Med. Chem. 20, 1482-93, (2012)

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Synthesis, stereoelectronic characterization and antiparasitic activity of new 1-benzenesulfonyl-2-methyl-1,2,3,4-tetrahydroquinolines. Romina J Pagliero et al Bioorg. Med. Chem. 18, 142-50, (2010)

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Antiprotozoal polyacetylenes from the Tanzanian medicinal plant Cussonia zimmermannii. Martin Senn et al J. Nat. Prod. 70, 1565-9, (2007)

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GS-9191 is a novel topical prodrug of the nucleotide analog 9-(2-phosphonylmethoxyethyl)guanine with antiproliferative activity and possible utility in the treatment of human papillomavirus lesions. Grushenka H I Wolfgang et al Antimicrob. Agents Chemother. 53, 2777-84, (2009)

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Synthesis and antiparasitic and antifungal evaluation of 2'-arylsubstituted-1H,1'H-[2,5']bisbenzimidazolyl-5-carboxamidines. Mehmet Alp et al Eur. J. Med. Chem. 44, 2002-8, (2009)

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Synthesis and antitrypanosomal evaluation of derivatives of N-benzyl-1,2-dihydroquinolin-6-ols: Effect of core substitutions and salt formation. Carolyn S Reid et al Bioorg. Med. Chem. 19, 513-23, (2011)

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Synthesis and antiprotozoal activity of pyridyl analogues of pentamidine. Svetlana M Bakunova et al J. Med. Chem. 52, 4657-67, (2009)

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Antiparasitic compounds from Cupania cinerea with activities against Plasmodium falciparum and Trypanosoma brucei rhodesiense. M Salomé Gachet et al J. Nat. Prod. 74, 559-66, (2011)

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Synthesis and in vitro antiprotozoal activities of water-soluble, inexpensive 3,7-bis(dialkylamino)phenoxazin-5-ium derivatives. Jian-Feng Ge et al J. Med. Chem. 51, 3654-8, (2008)

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Condyloma eradication: self-therapy with 0.15-0.5% podophyllotoxin versus 20-25% podophyllin preparations--an integrated safety assessment. Longstaff E and von Krogh G Regul Toxicol Pharmacol 33(2), 117-37, (2001)

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2-Hexadecynoic acid inhibits plasmodial FAS-II enzymes and arrests erythrocytic and liver stage Plasmodium infections. Deniz Tasdemir et al Bioorg. Med. Chem. 18, 7475-85, (2010)

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Antiplasmodial and cytotoxicity evaluation of 3-functionalized 2-azetidinone derivatives. Pardeep Singh et al Bioorg. Med. Chem. Lett. 21, 4561-3, (2011)

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Anticancer Properties of an Important Drug Lead Podophyllotoxin Can Be Efficiently Mimicked by Diverse Heterocyclic Scaffolds Accessible via One-Step Synthesis Magedov, I. V.; et al. J. Med. Chem. 54, 4234, (2011)

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Okundoperoxide, a bicyclic cyclofarnesylsesquiterpene endoperoxide from Scleria striatinux with antiplasmodial activity. Simon M N Efange et al J. Nat. Prod. 72, 280-3, (2009)

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Privileged structure-guided synthesis of quinazoline derivatives as inhibitors of trypanothione reductase. Andrea Cavalli et al Bioorg. Med. Chem. Lett. 19, 3031-5, (2009)

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?-Branched acyclic nucleoside analogues as inhibitors of Plasmodium falciparum dUTPase. Beatriz Baragaña et al Bioorg. Med. Chem. 19, 2378-91, (2011)

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Synthesis and antiprotozoal activities of dicationic bis(phenoxymethyl)benzenes, bis(phenoxymethyl)naphthalenes, and bis(benzyloxy)naphthalenes. Donald A Patrick et al Eur. J. Med. Chem. 44, 3543-51, (2009)

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Sarah Cannon Cancer Center Consensus Conference on Novel Developments with Podophyllotoxin Therapy. Semin. Oncol. 23(6 Suppl 13), 1-60, (1996)

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Podophyllotoxin in the treatment of genital warts. Beutner KR Curr. Probl. Dermatol. 24, 227-32, (1996)

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Podophyllotoxin derivatives VP-16 and VM-26. D'Incalci M and Garattini S Cancer Chemother. Biol. Response Modif. 9, 67-70, (1987)

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Podophyllotoxin derivatives VP-16 and VM-26. D'Incalci M and Garattini S Cancer Chemother. Biol. Response Modif. 10, 57-63, (1988)

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From podophyllotoxin glucoside to etoposide. Stähelin H and von Wartburg A Fortschr. Arzneimittelforsch. 33, 169-266, (1989)

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[Item 149--Epithelial and melanotic skin tumors: human papillomavirus (HPV) tumors]. Ann. Dermatol. Venereol. 139(11 Suppl), A144-9, (2012)

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Prevention and handling of acute allergic and infusion reactions in oncology. Joerger M Ann. Oncol. 23 Suppl 10, x313-9, (2012)

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Podophyllotoxin derivatives. D'Incalci M and Garattini S Cancer Chemother. Biol. Response Modif. 11, 82-9, (1990)

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[Review on biosynthesis of podophyllotoxin]. Lu W, Fu C, and Zhao Y Zhongguo Zhong Yao Za Zhi 36(9), 1109-14, (2011)

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Drugs that inhibit tubulin polymerization: the particular case of podophyllotoxin and analogues. Desbène S and Giorgi-Renault S Curr. Med. Chem. Anticancer Agents 2(1), 71-90, (2002)

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Spectrophotometric determination of drugs with iodine. Karuna T, et al. J. Sci. Ind. Res. 65(10), 808, (2006)

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Jacaranone-derived glucosidic esters from Jacaranda glabra and their activity against Plasmodium falciparum. M Salomé Gachet et al J. Nat. Prod. 73, 553-6, (2010)

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Synthesis and pharmacological evaluation of fluorescent and photoactivatable analogues of antiplasmodial naphthylisoquinolines. Gerhard Bringmann et al J. Med. Chem. 50, 6104-15, (2007)

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Podophyllotoxin, steganacin and combretastatin: natural products that bind at the colchicine site of tubulin. Sackett DL Pharmacol. Ther. 59(2), 163-228, (1993)

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Allogeneic stem cell transplantation for relapsed or refractory lymphoma after conditioning with BEAM/fludarabine/TBI. O'Meara A, Halter J, Heim D, et al. Biol. Blood Marrow Transplant. 19(1), 82-6, (2013)

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Discovery and development of natural product-derived chemotherapeutic agents based on a medicinal chemistry approach. Kuo-Hsiung Lee et al J. Nat. Prod. 73, 500-16, (2010)

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Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species. Denis Fourches et al Chem. Res. Toxicol. 23, 171-83, (2010)

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Discovery and investigation of antiproliferative and apoptosis-inducing properties of new heterocyclic podophyllotoxin analogues accessible by a one-step multicomponent synthesis. Igor V Magedov et al J. Med. Chem. 50, 5183-92, (2007)

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Synthesis and biological evaluation of novel thiocolchicine-podophyllotoxin conjugates. Daniele Passarella et al Eur. J. Med. Chem. 45, 219-26, (2010)

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Marinoquinolines A-F, pyrroloquinolines from Ohtaekwangia kribbensis (Bacteroidetes). Patrick W Okanya et al J. Nat. Prod. 74, 603-8, (2011)

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Endophyte fungal isolates from Podophyllum peltatum produce podophyllotoxin. Amy L Eyberger et al J. Nat. Prod. 69, 1121-4, (2006)

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Antiplasmodial and antitrypanosomal activities of aminobicyclo[2.2.2]octyl omega-aminoalkanoates. Christian Schlapper et al Eur. J. Med. Chem. 44, 736-44, (2009)

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Structural simplification of bioactive natural products with multicomponent synthesis. 2. antiproliferative and antitubulin activities of pyrano[3,2-c]pyridones and pyrano[3,2-c]quinolones. Igor V Magedov et al J. Med. Chem. 51, 2561-70, (2008)

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The chemical and biological route from podophyllotoxin glucoside to etoposide: ninth Cain memorial Award lecture. Stähelin HF and von Wartburg A Cancer Res. 51(1), 5-15, (1991)

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Synthesis and antiprotozoal activities of simplified analogs of naphthylisoquinoline alkaloids. Gerhard Bringmann et al Eur. J. Med. Chem. 43, 32-42, (2008)

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Inhibitors of tubulin polymerization: synthesis and biological evaluation of hybrids of vindoline, anhydrovinblastine and vinorelbine with thiocolchicine, podophyllotoxin and baccatin III. Daniele Passarella et al Bioorg. Med. Chem. 16, 6269-85, (2008)

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Synthesis and biological evaluation of 2-amino-3-(3',4',5'-trimethoxybenzoyl)-5-aryl thiophenes as a new class of potent antitubulin agents. Romeo Romagnoli et al J. Med. Chem. 49, 3906-15, (2006)

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Current status of podophyllotoxin for the treatment of genital warts. Beutner KR and von Krogh G Semin. Dermatol. 9(2), 148-51, (1990)

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Synthesis and structure-activity relationships of carbazole sulfonamides as a novel class of antimitotic agents against solid tumors. Laixing Hu et al J. Med. Chem. 49, 6273-82, (2006)

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Uncovering the origin of the black stains in Lascaux Cave in France. Saiz-Jimenez C, Miller AZ, Martin-Sanchez PM, et al. Environ. Microbiol. 14(12), 3220-31, (2012)

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QSAR guided synthesis of simplified antiplasmodial analogs of naphthylisoquinoline alkaloids. Gerhard Bringmann et al Eur. J. Med. Chem. 45, 5370-83, (2010)

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Polyalkoxybenzenes from plants. 5. Parsley seed extract in synthesis of azapodophyllotoxins featuring strong tubulin destabilizing activity in the sea urchin embryo and cell culture assays. Marina N Semenova et al J. Med. Chem. 54, 7138-49, (2011)

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Cytotoxic simplified tubulysin analogues. Bhooma Raghavan et al J. Med. Chem. 51, 1530-3, (2008)

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N-benzoylated phenoxazines and phenothiazines: synthesis, antiproliferative activity, and inhibition of tubulin polymerization. Helge Prinz et al J. Med. Chem. 54, 4247-63, (2011)

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Podophyllotoxin. Canel C, Moraes RM, Dayan FE, et al. Phytochemistry 54(2), 115-20, (2000)

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Synthesis and anticancer activity of 4?-alkylamidochalcone and 4?-cinnamido linked podophyllotoxins as apoptotic inducing agents. Ahmed Kamal et al Eur. J. Med. Chem. 47, 530-45, (2012)

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Genetic mapping of targets mediating differential chemical phenotypes in Plasmodium falciparum. Jing Yuan et al Nat. Chem. Biol. 5, 765-71, (2009)

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Antimalarial dual drugs based on potent inhibitors of glutathione reductase from Plasmodium falciparum. Wolfgang Friebolin et al J. Med. Chem. 51, 1260-77, (2008)

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Evaluation of azasterols as anti-parasitics. Ludovic Gros et al J. Med. Chem. 49, 6094-103, (2006)

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Podophyllotoxin derivatives: current synthetic approaches for new anticancer agents. You Y Curr. Pharm. Des. 11(13), 1695-717, (2005)

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Next generation sequencing in predicting gene function in podophyllotoxin biosynthesis. Marques JV, Kim KW, Lee C, et al. J. Biol. Chem. 288(1), 466-79, (2013)

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Antitumor properties of podophyllotoxin and related compounds. Gordaliza M, Castro MA, del Corral JM, et al. Curr. Pharm. Des. 6(18), 1811-39, (2000)

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Novel derivatives of 1,3,4-oxadiazoles are potent mitostatic agents featuring strong microtubule depolymerizing activity in the sea urchin embryo and cell culture assays. Alex S Kiselyov et al Eur. J. Med. Chem. 45, 1683-97, (2010)

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Camptothecin and podophyllotoxin derivatives: inhibitors of topoisomerase I and II - mechanisms of action, pharmacokinetics and toxicity profile. Hartmann JT and Lipp HP Drug Saf. 29(3), 209-30, (2006)

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Isoflavonoids and other compounds from Psorothamnus arborescens with antiprotozoal activities. Manar M Salem et al J. Nat. Prod. 69, 43-9, (2006)

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Synthesis and in vitro antiprotozoal activities of 5-phenyliminobenzo[a]phenoxazine derivatives. Xue-Liang Shi et al Bioorg. Med. Chem. Lett. 21, 5804-7, (2011)

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Synthesis of a new 4-aza-2,3-didehydropodophyllotoxin analogues as potent cytotoxic and antimitotic agents Kamal, A.; et al. Bioorg. Med. Chem. 19, 2349, (2011)

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Bis(oxyphenylene)benzimidazoles: a novel class of anti-Plasmodium falciparum agents. Annie Mayence et al Bioorg. Med. Chem. 19, 7493-500, (2011)

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Sulfonate derivatives of naphtho[2,3-b]thiophen-4(9H)-one and 9(10H)-anthracenone as highly active antimicrotubule agents. Synthesis, antiproliferative activity, and inhibition of tubulin polymerization. Anne Zuse et al J. Med. Chem. 50, 6059-66, (2007)

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Synthesis and biological evaluation of conjugates of deoxypodophyllotoxin and 5-FU as inducer of caspase-3 and -7. Wen-Ting Huang et al Eur. J. Med. Chem. 49C, 48-54, (2012)

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Podophyllotoxin: distribution, sources, applications and new cytotoxic derivatives. Gordaliza M, García PA, del Corral JM, et al. Toxicon 44(4), 441-59, (2004)

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Investigating new therapeutic strategies targeting hyperinsulinemia's mitogenic effects in a female mouse breast cancer model. Rostoker R, Bitton-Worms K, Caspi A, et al. Endocrinology 154(5), 1701-10, (2013)

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Synthesis and biological evaluation of novel conjugates of podophyllotoxin and 5-FU as antineoplastic agents. Shi-Wu Chen et al Bioorg. Med. Chem. 17, 3111-7, (2009)

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Design, synthesis and evaluation of novel uracil amino acid conjugates for the inhibition of Trypanosoma cruzi dUTPase. Orla K Mc Carthy et al Bioorg. Med. Chem. Lett. 16, 3809-12, (2006)

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Replacement of the lactone moiety on podophyllotoxin and steganacin analogues with a 1,5-disubstituted 1,2,3-triazole via ruthenium-catalyzed click chemistry. Daniela Imperio et al Bioorg. Med. Chem. 15, 6748-57, (2007)

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F14512, a polyamine-vectorized anti-cancer drug, currently in clinical trials exhibits a marked preclinical anti-leukemic activity. Kruczynski A, Pillon A, Créancier L, et al. Leukemia 27(11), 2139-48, (2013)

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Redox-active dinitrodiphenylthioethers against Leishmania: synthesis, structure-activity relationships and mechanism of action studies. Dawn A Delfín et al Bioorg. Med. Chem. 17, 820-9, (2009)

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Lignans from Dysosma versipellis with inhibitory effects on prostate cancer cell lines. Ren-Wang Jiang et al J. Nat. Prod. 70, 283-6, (2007)

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Synthesis and anticancer activity of heteroaromatic linked 4β-amido podophyllotoxins as apoptotic inducing agents. Kamal A, Tamboli JR, Vishnuvardhan MV, et al. Bioorg. Med. Chem. Lett. 23(1), 273-80, (2013)

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Biotechnological aspects of the production of the anticancer drug podophyllotoxin. Farkya S, Bisaria VS, and Srivastava AK Appl. Microbiol. Biotechnol. 65(5), 504-19, (2004)

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Synthesis and structure-activity relationship of 3-phenylquinoxaline 1,4-di-N-oxide derivatives as antimalarial agents. Esther Vicente et al Eur. J. Med. Chem. 43, 1903-10, (2008)

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Biological evaluation of glycosyl-isoindigo derivatives against the pathogenic agents of tropical diseases (malaria, Chagas disease, leishmaniasis and human African trypanosomiasis). Fadoua Bouchikhi et al Bioorg. Med. Chem. Lett. 21, 6319-21, (2011)

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10-(2-oxo-2-phenylethylidene)-10H-anthracen-9-ones as highly active antimicrotubule agents: synthesis, antiproliferative activity, and inhibition of tubulin polymerization. Helge Prinz et al J. Med. Chem. 52, 1284-94, (2009)

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Synthesis and cytotoxicity evaluation of novel 1,4-disubstituted 1,2,3-triazoles via CuI catalysed 1,3-dipolar cycloaddition. Jyothi Vantikommu et al Eur. J. Med. Chem. 45, 5044-50, (2010)

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Synthesis and biological evaluation of 4?-acrylamidopodophyllotoxin congeners as DNA damaging agents. Ahmed Kamal et al Bioorg. Med. Chem. 19, 4589-600, (2011)

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Studies on novel 4beta-[(4-substituted)-1,2,3-triazol-1-yl] podophyllotoxins as potential anticancer agents. Bilal A Bhat et al Eur. J. Med. Chem. 43, 2067-72, (2008)

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Temporal trends in genital warts among individuals covered by the public prescription drug insurance plan in the province of Quebec, Canada, from 1998 to 2007. Steben M, Ouhoummane N, Rodier C, et al. J. Low. Genit. Tract Dis. 17(2), 147-53, (2013)

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Irreversible inactivation of trypanothione reductase by unsaturated Mannich bases: a divinyl ketone as key intermediate. Brittany Lee et al J. Med. Chem. 48, 7400-10, (2005)

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An efficient one-pot synthesis of benzothiazolo-4?-anilino-podophyllotoxin congeners: DNA topoisomerase-II inhibition and anticancer activity. Ahmed Kamal et al Bioorg. Med. Chem. Lett. 21, 350-3, (2011)

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Benzoylphenylurea sulfur analogues with potent antitumor activity. Gurulingappa Hallur et al J. Med. Chem. 49, 2357-60, (2006)

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9-Benzylidene-naphtho[2,3-b]thiophen-4-ones as novel antimicrotubule agents-synthesis, antiproliferative activity, and inhibition of tubulin polymerization. Anne Zuse et al J. Med. Chem. 49, 7816-25, (2006)

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[4-(imidazol-1-yl)thiazol-2-yl]phenylamines. A novel class of highly potent colchicine site binding tubulin inhibitors: synthesis and cytotoxic activity on selected human cancer cell lines. Siavosh Mahboobi et al J. Med. Chem. 49, 5769-76, (2006)

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Synthesis of 4?-triazole-podophyllotoxin derivatives by azide-alkyne cycloaddition and biological evaluation as potential antitumor agents. Hong Chen et al Eur. J. Med. Chem. 46, 4709-14, (2011)

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Gallic acid-based indanone derivatives as anticancer agents. Hari Om Saxena et al Bioorg. Med. Chem. Lett. 18, 3914-8, (2008)

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CHMIS-C: a comprehensive herbal medicine information system for cancer. Xueliang Fang et al J. Med. Chem. 48, 1481-8, (2005)

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Protective effects and mechanisms of curcumin on podophyllotoxin toxicity in vitro and in vivo. Li J, Dai CX, Sun H, et al. Toxicol. Appl. Pharmacol. 265(2), 190-9, (2012)

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Synthesis and biological evaluation of new podophyllic aldehyde derivatives with cytotoxic and apoptosis-inducing activities. Ma Angeles Castro et al J. Med. Chem. 53, 983-93, (2010)

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Structural characterization of a recombinant fusion protein by instrumental analysis and molecular modeling. Wu Z, Zhou P, Li X, et al. PLoS ONE 8(3), e57642, (2013)

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Synthesis and biological evaluation of a series of podophyllotoxins derivatives as a class of potent antitubulin agents. Liu Y, Wei D, Zhao Y, et al. Bioorg. Med. Chem. 20(21), 6285-95, (2012)

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Podophyllotoxin directly binds a hinge domain in E2 of HPV and inhibits an E2/E7 interaction in vitro. Takeki Saitoh et al Bioorg. Med. Chem. 16, 5815-25, (2008)

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Proteomic changes induced by podophyllotoxin in human cervical carcinoma HeLa cells. Wang B, Chen L, Zhen H, et al. Am. J. Chin. Med. 41(1), 163-75, (2013)

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Ultrahigh pressure extraction of lignan compounds from Dysosma versipellis and purification by high-speed counter-current chromatography. Zhu Q, Liu F, Xu M, et al. J. Chromatogr. B. Analyt. Technol. Biomed. Life Sci. 905, 145-9, (2012)

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Synthesis, biological evaluation, and molecular modeling of 3,5-substituted-N1-phenyl-N4,N4-di-n-butylsulfanilamides as antikinetoplastid antimicrotubule agents. Tesmol G George et al Bioorg. Med. Chem. 15, 6071-9, (2007)

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Cytotoxic lignans from fruits of Cleistanthus indochinensis: synthesis of cleistantoxin derivatives. Thanh VT, Pham VC, Mai HD, et al. J. Nat. Prod. 75(9), 1578-83, (2012)

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Novel potent antimitotic heterocyclic ketones: synthesis, antiproliferative activity, and structure-activity relationships. Laixing Hu et al Bioorg. Med. Chem. Lett. 17, 3613-7, (2007)

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Synthesis and anti-HIV-1 activities of novel podophyllotoxin derivatives. Shi-Wu Chen et al Bioorg. Med. Chem. Lett. 17, 2091-5, (2007)

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Adva-27a, a novel podophyllotoxin derivative found to be effective against multidrug resistant human cancer cells. Merzouki A, Buschmann MD, Jean M, et al. Anticancer Res. 32(10), 4423-32, (2012)

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Synthetic and application perspectives of azapodophyllotoxins: alternative scaffolds of podophyllotoxin. Kumar A, Kumar V, Alegria AE, et al. Curr. Med. Chem. 18(25), 3853-70, (2011)

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Three new cytotoxic aryltetralin lignans from Sinopodophyllum emodi. Yan-Jun Sun et al Bioorg. Med. Chem. Lett. 21, 3794-7, (2011)

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Synthesis, antiproliferative activity and inhibition of tubulin polymerization by anthracenone-based oxime derivatives. Georg Surkau et al Eur. J. Med. Chem. 45, 3354-64, (2010)

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Structural simplification of bioactive natural products with multicomponent synthesis: dihydropyridopyrazole analogues of podophyllotoxin. Igor V Magedov et al Bioorg. Med. Chem. Lett. 17, 1381-5, (2007)

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Conformationally restricted analogs of Combretastatin A-4 derived from SU5416. Pui-Kai Li et al Bioorg. Med. Chem. Lett. 15, 5382-5, (2005)

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Phenylimino-10H-anthracen-9-ones as novel antimicrotubule agents-synthesis, antiproliferative activity and inhibition of tubulin polymerization. Helge Prinz et al Bioorg. Med. Chem. 19, 4183-91, (2011)

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Anti-malarial activity of N6-modified purine analogues. Kathleen Too et al Bioorg. Med. Chem. 15, 5551-62, (2007)

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Novel linear and step-gradient counter-current chromatography for bio-guided isolation and purification of cytotoxic podophyllotoxins from Dysosma versipellis (Hance). Yang Z, Liu X, Wang K, et al. J. Sep. Sci. 36(6), 1022-8, (2013)

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Novel pyridinyl and pyrimidinylcarbazole sulfonamides as antiproliferative agents. Laixing Hu et al Bioorg. Med. Chem. Lett. 17, 1193-6, (2007)

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Novel three-component synthesis and antiproliferative properties of diversely functionalized pyrrolines. Igor V Magedov et al Bioorg. Med. Chem. Lett. 18, 1392-6, (2008)

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Phase II trial of 131-Iodine tositumomab with high-dose chemotherapy and autologous stem cell transplantation for relapsed diffuse large B cell lymphoma. Vose JM, Bierman PJ, Loberiza FR, et al. Biol. Blood Marrow Transplant. 19(1), 123-8, (2013)

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Synthesis and cytotoxic evaluation of C-9 oxidized podophyllotoxin derivatives. Ma Angeles Castro et al Bioorg. Med. Chem. 15, 1670-8, (2007)

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Synthesis, characterization and in vitro biological evaluation of some novel diarylsulfonylureas as potential cytotoxic and antimicrobial agents. Vasudeva Rao Avupati et al Bioorg. Med. Chem. Lett. 22, 1031-5, (2012)

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Reengineered epipodophyllotoxin. Magedov IV, Evdokimov NM, Karki M, et al. Chem. Commun. (Camb.) 48(84), 10416-8, (2012)

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Synthesis, antiproliferative activity and inhibition of tubulin polymerization by 1,5- and 1,8-disubstituted 10H-anthracen-9-ones bearing a 10-benzylidene or 10-(2-oxo-2-phenylethylidene) moiety. Holger C Nickel et al Eur. J. Med. Chem. 45, 3420-38, (2010)

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Star-shaped polycaprolactone-polyethyleneglycol copolymer micelle-like nanoparticles for picropodophyllin delivery. Zhao J, Wang Y, and Luan L J. Biomed. Nanotechnol. 10(8), 1627-34, (2014)

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Interplay of reactive oxygen species, intracellular Ca2+ and mitochondrial homeostasis in the apoptosis of prostate cancer cells by deoxypodophyllotoxin. Kim KY, Cho HJ, Yu SN, et al. J. Cell. Biochem. 114(5), 1124-34, (2013)

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Discovery of novel and potent benzhydryl-tropane trypanocides highly selective for Trypanosoma cruzi. G A Holloway et al Bioorg. Med. Chem. Lett. 20, 1816-8, (2010)

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Structure-activity relationship studies on a novel class of antiproliferative agents derived from Lavendustin A. Part I: Ring A modifications. Peter Nussbaumer et al Bioorg. Med. Chem. 16, 7552-60, (2008)

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Cytotoxic podophyllotoxin type-lignans from the steam bark of Bursera fagaroides var. fagaroides. Rojas-Sepúlveda AM, Mendieta-Serrano M, Mojica MY, et al. Molecules 17(8), 9506-19, (2012)

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Picropodophyllin inhibits epithelial ovarian cancer cells in vitro and in vivo. Lu X, Wang L, Mei J, et al. Biochem. Biophys. Res. Commun. 435(3), 385-90, (2013)

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Alkyl-linked bis-THTT derivatives as potent in vitro trypanocidal agents. Julieta Coro et al Bioorg. Med. Chem. Lett. 16, 1312-5, (2006)

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Podophyllotoxin analogues active versus Trypanosoma brucei. Md Jashim Uddin et al Bioorg. Med. Chem. Lett. 20, 1787-91, (2010)

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Humibacter antri sp. nov., an actinobacterium isolated from a natural cave, and emended description of the genus Humibacter. Lee SD Int. J. Syst. Evol. Microbiol. 63(Pt 11), 4315-9, (2013)

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3-(2'-Bromopropionylamino)-benzamides as novel S-phase arrest agents. Laixing Hu et al Bioorg. Med. Chem. Lett. 17, 6847-52, (2007)

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Abnormal expression of insulin-like growth factor-I receptor in hepatoma tissue and its inhibition to promote apoptosis of tumor cells. Dong Z, Yao M, Wang L, et al. Tumour Biol. 34(6), 3397-405, (2013)

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Young women's experiences of managing self-treatment for anogenital warts. Hammarlund K, Nyström M, and Jomeen J Sex. Reprod. Healthc. 3(3), 117-21, (2012)

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Picropodophyllin inhibits tumor growth of human nasopharyngeal carcinoma in a mouse model. Yin SC, Guo W, and Tao ZZ Biochem. Biophys. Res. Commun. 439(1), 1-5, (2013)

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Design, synthesis, and antitumor activity of novel podophyllotoxin derivatives as potent anticancer agents. Liu J, Cao B, Gao Y, et al. J. Asian Nat. Prod. Res. 15(9), 985-92, (2013)

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Antifeedant activity of spin-labeled derivatives of deoxypodophyllotoxin against Brontispa longissima larvae. Feng G, Zhang J, Yang L, et al. Nat. Prod. Commun. 8(2), 199-202, (2013)

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[A model-based comparison of cost effectiveness of imiquimod versus podophyllotoxin for the treatment of external anogenital warts in France]. Lafuma A, Monsonego J, Moyal-Barracco M, et al. Ann. Dermatol. Venereol. 130(8-9 Pt 1), 731-6, (2003)

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Safety and activity of a new intensive short-term chemoimmunotherapy in HIV-positive patients with Burkitt lymphoma. Ferreri AJ, Bruno Ventre M, Donadoni G, et al. Br. J. Haematol. 159(2), 252-5, (2012)

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Merck 14,7546

Beil. 19,V,10,666

Aldrich MSDS 1, 1507:A / Corp MSDS 1 (2), 2857:B / FT-IR 2 (2), 2900:A / FT-IR 1 (2), 320:A / FT-NMR 1 (2), 1304:A / IR-Spectra (3), 1042:E / IR-Spectra (2), 911:G / RegBook 1 (2), 1937:I / Sigma FT-IR 1 (1), 572:D / Structure Index 1, 311:B:7

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